2,6-Dichlorophenyl-substituted amino-imidazole derivatives and use as hypertensive agents

US4275072A · kind A · utility

Assignee

• Farmos Group Ltd. · FI

Inventors

• Arto Karjalainen · Oulu, FI
• Kauko O. A. Kurkela · Espoo, FI

Key dates

• Filing date: Nov 13, 1979
• Grant date: Jun 23, 1981
• Expiry date: Nov 13, 1999

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D233/88
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The 2,6-dichlorophenyl-substituted amino-imidazole derivatives 1-(2',6'-dichlorophenyl)-2-amino-4-methyl-imidazole, 2-(2',6'-dichloroanilino)-4-methyl-imidazole, their non-toxic, pharmaceutically acceptable, acid addition salts and mixtures thereof, exhibit excellent anti-hypertensive activity which makes the derivatives particularly suitable for treatment of high blood pressure in mammals. The derivatives may be prepared in either of two processes. The first process involves the sequential reaction of a known starting material with ammonia and a halogenated acetone which may be followed by separation of the formed isomers. The second process involves the decarboxylation of the novel intermediates 4-[1-(2',6'-dichlorophenyl)-2-amino)]-imidazoleacetic acid or 4-[2-(2',6'-dichloroanilino)]-imidazoleacetic acid or mixtures thereof. Such intermediates, their lower alkyl esters, their non-toxic, pharmaceutically acceptable acid addition salts or mixtures thereof may also be employed as a diuretic agent. The derivatives are employed in an effective amount and are typically combined with a pharmaceutical carrier. Administration of the derivatives may be accomplished either orally or paren…